US5534050A - Thermal ink jet composition - Google Patents

Thermal ink jet composition Download PDF

Info

Publication number
US5534050A
US5534050A US08450075 US45007595A US5534050A US 5534050 A US5534050 A US 5534050A US 08450075 US08450075 US 08450075 US 45007595 A US45007595 A US 45007595A US 5534050 A US5534050 A US 5534050A
Authority
US
Grant status
Grant
Patent type
Prior art keywords
ink jet
ink
wt
jet printing
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US08450075
Inventor
Kurt B. Gundlach
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Samsung Electronics Co Ltd
Original Assignee
Xerox Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Grant date

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/30Inkjet printing inks
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2609Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/60Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing acetylenic group

Abstract

A thermal ink jet printing composition contains an acetylenic polyalkylene oxide and a quasisurfactant penetrant.

Description

BACKGROUND OF THE INVENTION

The invention relates to a thermal ink jet composition, a printing process and a method of improving the fast dry characteristics of inks.

Ink jet printing systems generally are of two types: continuous stream and drop-on-demand. In continuous stream ink jet systems, ink is emitted in a continuous stream under pressure through at least one orifice or nozzle. The stream is perturbed, causing it to break up into droplets at a fixed distance from the orifice. At the break-up point, the droplets are charged in accordance with digital data signals and passed through an electrostatic field that adjusts the trajectory of each droplet in order to direct it to a gutter for recirculation or to a specific location on a recording medium. In drop-on-demand systems, a droplet is expelled from an orifice directly to a position on a recording medium in accordance with digital data signals. A droplet is not formed or expelled unless it is to be placed on the recording medium.

Quality thermal ink jet printing can be achieved by utilizing an aqueous ink composition containing at least one dye or pigment, a wetting agent and water. U.S. Pat. No. 4,508,570 to Fujii et al., discloses an aqueous ink for ink jet printing, which comprises a water-soluble direct dye and/or acid dye, a polyhydric alcohol and/or an alkyl ether thereof, water, and at least one water-soluble non-ionic surface active agent selected from a specified polyoxyethylene alkyl amine, a specified polyoxyethylene alkyl phenyl ether and a specified polyoxyethylene alkyl ether. U.S. Pat. No. 4,623,689 to Shintani et al., discloses an ink jet ink containing aqueous colored polymers, which comprise a homopolymer of an ethylenically unsaturated sulfonic acid or its salt or a copolymer of an ethylenically unsaturated sulfonic acid or its salt with another ethylenically unsaturated monomer, wherein the homopolymer or copolymer is dyed with a basic dye and has a lowest film-forming temperature of not higher than 35° C. U.S. Pat. No. 4,627,876 to Fries et al., discloses a printing ink containing a pigment and an alkyd resin binder. The resin binder is modified with fatty acids. The alkyd resin is the reaction product of (a) a fatty acid, triglyceride of a fatty acid or a mixture of fatty acids, (b) a polyol, (c) an epoxy resin and (d) a dicarboxylic acid.

U.S. Pat. No. 4,026,713 to Sambucetti et al. relates to a magnetic ink containing non-ionic, cationic and/or anionic surfactants. The surfactants may include glycerol, a lower alkyl monoether of ethylene glycol and/or a polyethylene diol.

U.S. Pat. No. 4,914,562 to Abe et al. discloses an ink jet composition containing an ionic surface active agent or a non-ionic surface active agent. The ionic surface active agent can be a dioctyl sulfosuccinate sodium salt, sodium oleate or dodecylbenzenesulfonic acid. The non-ionic surface active agent may be diethylene glycol mono-n-butyl ether or triethylene glycol mono-n-butyl ether.

U.S. Pat. No. 5,019,166 to Schwarz relates to a thermal ink jet printing composition comprising a dye, a liquid medium and a surfactant selected from the group consisting of polyoxyalkylated ethers, anionic bitail fluorothio alkyls, alkyl aryl sulfonates, alkyl amine quaternary salts and mixtures thereof.

U.S. Pat. No. 5,116,409 to Moffatt discloses a process for reducing color bleed of inks employed in thermal ink jet printing. The process comprises printing two inks side by side, each ink having a composition comprising (a) a vehicle and (b) about 0.1 to 10 wt. % of at least one water-soluble anionic dye. The vehicle comprises at least one member selected from the group consisting of zwitterionic surfactants and non-ionic amphiphiles and water or water and an organic solvent. Moffatt discloses a composition that includes SURFYNOL S465, an acetylenic polyethylene oxide, and 1,5-pentanediol.

U.S. Pat. No. 5,254,159 to Gundlach et al. discloses an ink composition that comprises water, an anionic dye and an amine compound. The ink composition provides waterfast images. The disclosure of this patent is incorporated in its entirety herein by reference.

Full color printing in a thermal ink jet printing process requires an ink with fast dry characteristics. Fast dry characteristics can be improved by the addition of a penetrant. The penetrant can be a quasisurfactant penetrant. For the purposes of this invention, a quasisurfactant penetrant is a surfactant that is substituted with a polar substituent toward one end of a chain of 4-8 aliphatic carbon atoms. Exemplary penetrants include dl-1,2-hexanediol, 1,2-octanediol, diethylene glycol monobutyether, 1-cyclohexyl-2-pyrrolidinone, 2-methyl-2-propyl-1,3-propanediol and 1-butanesulfonic acid sodium salt.

A penetrant imparts quick-dry characteristics to a thermal ink jet ink composition. However, effectiveness of a penetrant in providing quick-dry characteristics varies with ink composition solvent. Some penetrants do not provide acceptable quick-dry characteristics to some ink-solvent systems. Cosolvents can be added to ink compositions to improve effectiveness of the surfactant penetrant or penetrant concentration in the ink compositions can be increased to achieve satisfactory quick-dry characteristics. However, some cosolvent packages and/or higher penetrant concentrations cause deterioration of thermal ink jet hardware. For example, higher loads of butylcarbitol or higher loads of cyclohexyl pyrrolidinone aggressively attack cartridge materials and seals.

SUMMARY OF THE INVENTION

The present invention relates to an improved thermal ink jet printing composition containing a surfactant comprising an acetylenic polyalkylene oxide and a quasisurfactant penetrant.

The combination of an acetylenic polyethylene glycol with a quasisurfactant penetrant provides a universally applicable surfactant package. The use of either surfactant alone does not provide an ink with the fast dry characteristics that are required for full color thermal ink jet printing. Unexpectedly, the combination of an acetylenic polyethylene oxide and a quasisurfactant penetrant results in an ink that gives acceptable rapid dry characteristics. Additionally, the combination unexpectedly provides rapid dry characteristics independent of the ink vehicle co-solvent. Fast dry, full color ink sets can be provided by the present invention without high loads of additives that deteriorate thermal ink jet hardware materials.

The present invention also relates to a thermal ink jet printing process comprising causing an ink jet composition comprising an acetylenic polyethylene oxide and a quasisurfactant penetrant to be injected in an image wise fashion from a thermal ink jet printer onto a substrate.

Finally, the present invention is directed to a method of improving fast dry characteristics of thermal ink jet inks comprising incorporating into a thermal ink jet composition, a combination of an acetylenic polyethylene oxide and a quasisurfactant penetrant.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

Inks of the present invention comprise a dye colorant. Generally, any effective dye, such as one of the direct dyes or the acid dyes, may be selected, provided that the dye is compatible with the other ink components and is soluble in the liquid medium.

Examples of suitable dyes include Bernacid Red 2BMN; Pontamine Brilliant Bond Blue A; BASF X-34; Pontamine; Food Black 2; Carodirect Turquoise FBL Supra Conc. (Direct Blue 199), available from Carolina Color and Chemical; Special Fast Turquoise 8GL Liquid (Direct Blue 86), available from Mobay Chemical; Intrabond Liquid Turquoise GLL (Direct Blue 86), available from Crompton and Knowles; Cibracron Brilliant Red 38-A (Reactive Red 4), available from Aldrich Chemical; Drimarene Brilliant Red X-2B (Reactive Red 56), available from Pylam, Inc.; Levafix Brilliant Red E-4B, available from Mobay Chemical; Levafix Brilliant Red E6BA, available from Mobay Chemical; Procion Red H8B (Reactive Red 31), available from ICI America; Pylam Certified D&C Red #28 (Acid Red 92), available from Pylam; Direct Brill Pink B Ground Crude, available from Crompton & Knowles; Cartasol Yellow GTF Presscake, available from Sandoz, Inc.; Tartrazine Extra Conc. (FD&C Yellow #5, Acid Yellow 23), available from Sandoz; Carodirect Yellow RL (Direct Yellow 86), available from Carolina Color and Chemical; Cartasol Yellow GFT Liquid Special 110, available from Sandoz, Inc.; D&C Yellow #10 (Acid Yellow 3), available from Tricon; Yellow Shade 16948, available from Tricon, Basacid Black X34, available from BASF, Carta Black 2GT, available from Sandoz, Inc.; Neozapon Red 492 (BASF); Orasol Red G (Ciba-Geigy); Direct Brilliant Pink B (Crompton-Knolls); Aizen Spilon Red C-BH (Hodagaya Chemical Company); Kayanol Red 3BL (Nippon Kayaku Company); Levanol Brilliant Red 3BW (Mobay Chemical Company); Levaderm Lemon Yellow (Mobay Chemical Company; Spirit Fast Yellow 3G; Aizen Spilon Yellow C-GNH (Hodagya Chemical Company); Sirius Supra Yellow GD 167; Cartasol Brilliant Yellow 4GF (Sandoz); Pergasol Yellow CGP (Ciba-Geigy); Orasol Black RL (Ciba-Geigy); Orasol Black RLP (Ciba-Geigy); Savinyl Black RLS (Sandoz); Dermacarbon 2GT (Sandoz); Pyrazol Black BG (ICI); Morfast Black Conc A (Morton-Thiokol); Diazol Black RN Quad (ICI); Orasol Blue GN (Ciba-Geigy); Savinyl Blue GLS (Sandoz); Luxol Blue MBSN (Morton-Thiokol); Severon Blue 5GMF (ICI); Basacid Blue 750 (BASF); and the like. Typical preferred dyes include Bernacid Red, available from Berncolors, Poughkeepsie, N.Y., Pontamine Brilliant Bond Blue, Berncolor A. Y. 34, Basacid Black X34, Carta Black 2 GT, Telon Fast Yellow 4GL-175, and the Like. The dye is generally present in the ink composition in an effective amount, generally from about 0.5 to about 8 percent by weight, and preferably from about 1 to about 6 percent by weight.

The inks of the present invention also include a liquid medium. Frequently, water comprises the major portion of the liquid medium and, while it may comprise 100 percent of the liquid medium, water is generally present in an amount of from about 7 to about 93 percent by weight of the ink, and preferably from about 55 to about 85 percent by weight of the ink.

Preferably, the inks of the present invention also contain a humectant such as a glycol, including ethylene glycol, propylene glycol, other glycols, or other known humectants as part of the liquid medium. When present, the humectant is present in an effective amount, generally from about 5 to about 60 percent by weight, preferably from about 10 to about 20 percent by weight, and most preferably at about 17 percent by weight. Any other suitable liquid medium can also be employed provided that the objectives of the present invention are achieved.

Optionally, the ink composition can include a biocide such as sorbic acid, 1 -(3-chloroallyl)-3,5,7-triaza- 1-azoniaadamantane chloride, commercially available as Dowicil 200 (Dow Chemical Company, Midland, Mich.), vinylene-bis thiocyanate, commercially available as Dowicil 200 (Dow Chemical Company, Midland, Mich.), vinylene-bis thiocyanate, commercially available as Cytox 3711 (American Cyanamid Company, Wayne, N.J.), disodium ethylenebisdithiocarbamate, commercially available as Dithone D14 (Rohm & Haas Company, Philadelphia, Pa.), bis(trichloromethyl) sulfone, commercially available as Biocide N-1386 (Stauffer Chemical Company, Westport, Conn.), zinc pyridinethione, commercially available as zinc omadine (Olin Corporation Stamford, Conn.), 2-bromo-t-nitropropane-1,3-diol, commercially available as onyxide 500 (Onyx Chemical Company, Jersey City, N.J.), Bosquat MB50 (Louza, Inc., Fairtown, N.J.) and the like may be present in the inks of the present invention. When present the biocide is in an effective amount, generally from about 0.01 to about 1 percent by weight, and preferably from about 0.1 to about 0.5 percent by weight.

The surfactant of the present invention comprises an acetylenic polyalkylene oxide and a quasisurfactant penetrant. The alkylene groups of the acetylenic polyalkylene oxides have two to four carbon atoms. Preferably the acetylenic polyalkylene oxides are acetylenic polyethylene oxides. The preferred acetylenic polyethylene oxides are ethoxylated tetramethyl decynediols such as the Surfynols manufactured by Air Products and Chemicals Inc. The Surfynols are represented as ##STR1## where n+m=0 to 50.

Effectiveness of penetrants in providing quick-dry characteristics varies with ink composition solvent. Significantly high loads of solvents such as butylcarbitol or cyclohexyl pyrrolidinone are usually required in order to achieve satisfactory high dry times for competitive thermal jet inks. Such solvent/penetrant systems aggressively attack hardware of an ink jet printer including the cartridge materials and seals. The present invention provides a surfactant comprising the combination of an acetylenic polyethylene oxide and a quasisurfactant penetrant that permits a surfactant load as low as 2.5 wt. %. Even at such low weight percent loads, thermal ink jet inks according to the present invention provide fast-dry characteristics. Additionally, the fast-dry characteristics obtained by the combination of surfactants of the invention are independent of the solvent selected for the ink.

Additional advantages of the combination surfactant of the present invention include improved solid area covering quality, elimination of decapped front face ink cartridge "weep" and improved print cartridge decapped print recoverability. Decapped face ink "weep" can occur when a print cartridge is left open and ink floods out of nozzles onto the cartridge front face plate. In one test for "weep," a cartridge is removed from a printer and the front face of the cartridge is cleaned with a vacuum wand. The cartridge is then permitted to set uncapped to evaporate ink from nozzle orifices. "Weep" occurs when the ink does not evaporate but rather oozes from nozzles and forms a crystalline ink deposit on the cartridge front face. "Decapped recoverability" describes the quality of print provided after the cartridge is replaced into the printer. Immediate recoverability means that the cartridge immediately begins to print clearly in acceptable quality.

Ethylene glycol, trimethylol propane, sulfolane, n-methylpyrrolidinone, thiodiethanol and glycerine have been found to be suitable cosolvents with the combination surfactant of the present invention. The ink jet inks of the present invention can comprise 0.1 to 2 wt. % acetylenic polyalkylene oxide and 0.2 to 8 wt. % quasisurfactant penetrant. Preferably the compositions contain 0.2 to 1 wt. % acetylenic polyalkylene oxide and 0.5 to 5 wt. % quasisurfactant penetrant. Most preferred is a composition containing 0.3 to 0.6 wt. % acetylenic polyalkylene oxide and 1 to 4 wt. % 1,2-hexanediol.

The ink compositions of the present invention are of a viscosity suitable for use in thermal ink jet printing processes. Typically, the ink viscosity is no more than about 5 centipoise, and preferably is from about 1 to about 2.5 centipoise.

Ink compositions of the present invention can be prepared by any suitable process. Typically, the inks are prepared by simple mixing of ingredients. One process entails mixing all of the ink ingredients together and filtering the mixture to obtain an ink. The inks of the present invention can be prepared by mixing ingredients, heating if desired, and filtering, followed by adding the acetylenic polyethylene oxide and quasisurfactant penetrant of the present invention to the mixture and mixing at room temperature with moderate shaking until a homogeneous mixture is obtained, typically from about 5 to about 10 minutes. Alternatively, the acetylenic polyethylene oxide and quasisurfactant penetrant of the present invention can be mixed with the other ink ingredients during the ink preparation process.

Ink pH is adjusted to a desired level at some time during the preparation process; typically, pH adjustment occurs subsequent to most of the other ink preparation steps by addition of an acid and a buffer, and preferably the pH adjustment occurs prior to filtration so that any solid precipitates generated by pH adjustment can be removed from the ink during the filtration step.

The present invention is also directed to a process that comprises incorporating an ink composition of the present invention into an ink jet printing apparatus and causing droplets of the ink composition to be ejected in an imagewise pattern onto a substrate. In an embodiment of the invention, the printing apparatus employs a thermal ink jet process wherein the ink in nozzles is selectively heated thereby causing droplets of the ink to be ejected in an imagewise pattern.

The printing process of the invention can be employed on any suitable substrate, including plain papers such as Xerox® 4024 papers, ruled notebook paper, bond paper, silica coated papers such as Sharp Company silica coated paper, JuJo paper, and the like, transparency materials, fabrics, textile products, plastic, polymeric films and inorganic substrates such as metals and wood, and the like. In one embodiment, the process comprises printing onto a porous or ink absorbent substrate, such as plain paper.

The invention will further be illustrated in the following, non-limiting examples, it being understood that these examples are intended to be illustrative only and that the invention is not intended to be limited to the materials, conditions, process parameters and the like recited therein.

EXAMPLE 1

In a bottle, are mixed 129.63 grams of deionized water, 40 grams of ethylene glycol, 4 grams of dl-1-2-hexanediol and 0.0603 gram of a polyethylene oxide/bisphenol A adduct. 0.195 grams of Dowicil is added to the mixture and the bottle is placed on a roll mill for 10 minutes. Thereafter, 4.01 grams of triethanolamine (from Aldrich Chemical Co.) is added to the bottle and the pH is adjusted to 7.5 with a 70% solution of H3PO3. Thereafter, 1.12 grams of Neolan Red EXB (C.J. Acid Red 52) and 4.52 grams of Duasyn Brilliant Red F38-SF VP218 (Reactive Red 180) are added to the bottle and the bottle is again placed on the roll mill for 30 minutes.

Dry time of the resulting ink is determined by a wire wand bar draw down test. A wand with a wrapped no. 6 wire saturated with ink composition is drawn down a paper to deposit ink. A standard wire wand draw down test indicates a satisfactory dry time of 35 seconds for the deposited ink prepared in this Example.

SURFYNOL 440 surfactant (ethoxylated tetramethyl decynediol), 0.99 grams, is added to the ink and pH is adjusted to 7.6. The total weight of the ink composition is 185.23 grams. 14.77 grams of deionized water is added to bring the weight to 200 grams and the ink is roll milled for an additional 10 minutes. Filter time of the ink composition with a 0.2 micron ink filter at 60 psi pressure is 330 seconds. The ink produces a vigorous bubble and the filter is clean. 50 grams of the ink is loaded into a Korvel print cartridge and the cartridge is placed in a Xerox printer, XPP4004. In operation, the printer immediately prints clear characters. Print dry time as tested on Cortland 4024DP felt paper is 0.5 seconds. After printing, the print cartridge is removed, decapped and set uncapped for a period of one day. No ink weep is noted. All jets of the print cartridge immediately print when the cartridge is replaced into the Xerox printer XP4004. The ink is tested for flow on a Xerox thermal ink jet transparency. The ink provides good solid area coverage on the transparency. Only slight curl is noted of an air dried solid print area.

The ink composition, method of preparing the composition and test results are summarized in Table 1.

                                  TABLE I__________________________________________________________________________INGREDIENT/DESCRIPTION        VENDOR     AMOUNT (GM)                                             SOL N                                                   MOLE__________________________________________________________________________                                                   EQVWATER                         103        129.63   NAETHYLENE GLYCOL               PETROCHEM  40       20DL-1,2-HEXANEDIOL             ALDRICH    4        2PEO                           POLYSCIENCE                                    0.0603   0.03  NADOWICIL, ROLL MILL 10 MINUTES, HOMOGENEOUS                         DOW        0.1995   0.1TRIETHANOLAMINE (TEA)         ALDRICH    4.01     2pH = 9.94, 70% H3PO3 pH = 7.50                         RHONE POULENC                                    1.11NEOLAN RED EXB (C.J. ACID RED 52)                         CIBA-GEIGY 1.12     0.6DUASYN BRILLIANT RED F38-SF VP218 (REACTIVE                         HEOSCHT    4.52     2.25  1RED 180)ROLL MILL 30 MINUTES, LOW FOAM                         NA         NA       NA    NA#6 WWB DRAW DOWN ON DRY TIME = 35 SECONDS                         NA         NA       NA    NASURFYNOL 440 SURFACTANT (ETHOXYLATED                         AIR PRODUCTS                                    0.99     0.5TETRAMETHYL DECYNEDIOL)pH = 7.60                     NA         NA       NA    NAINK WEIGHT = 185.23 GM, RO WATER TO 200 GM INK,                         103        14.77ROLL MILL 10 MINHOMOGENEOUS, FILTER 0.2       NA         NA       NA    NA__________________________________________________________________________ 200 GM INK FILTER TIME 0.2 MICRON 60 PSI = 330 SECONDS, VIGOROUS BUBBLE, CLEAN FILTER. LOADED KORBEL PRINT CARTRIDGE WITH 50 GM INK IMMEDIATELY PRINTED IN XPP4004. XPP4004 DRY TIME ON COURTLAND FELT = 0.5 SECONDS. RECOVERABILITY AFTER 1 DAY DECAPPED THEN IN XPP4004 BIPASSING LOAD PRIME IMMEDIATE ALL JETS. NO INK WEEP NOTED. GOOD SOLID AREA COVERAGE ON XEROX TRANSPARENCY; SLIGHT CURL OF AIR DRIED SOLID AREA PRINT.
COMPARATIVE EXAMPLES

Four inks are prepared according to the procedure of Example I The inks contain 20 wt. % ethylene glycol. A first ink is prepared without penetrant. A second ethylene glycol ink is prepared with a 2 wt. % load of 1,2-hexanediol. A third ink is prepared containing SURFYNOL 440 (ethoxylated tetramethyl decynediol by Air Products and Chemicals Inc). A fourth ink is prepared containing both 1,2-hexanediol and SURFYNOL 440.

The 20 wt. % ethylene glycol ink exhibits a dry time on Courtland 4024 paper of 120 seconds. When a 2 wt. % load of 1,2-hexanediol is added, dry time drops to 35 seconds. The addition of SURFYNOL 440 to the ethylene glycol ink reduces dry time to 3 seconds. Higher loadings of either the 1,2-hexanediol alone or the ethoxylated tetramethyl decynediol alone do not yield an ink with a dry time under 1 second. However, a combination of 2 wt. % of 1,2-hexanediol with 0.5 wt. % of ethoxylated tetramethyl decynediol in a 20 wt. % ethylene glycol system results in an ink that exhibits a dry time of 0.5 seconds on Courtland 2040DP paper.

EXAMPLES II-IX

Ink compositions are prepared according to the descriptions in the following Tables II-IX. The compositions are tested for filter time, dry time, decap recoverability and transparency coverage with the results as summarized after each table. In the tables RO Water is deionized water, GM is grams and PEO is a polyethylene oxide/bisphenol A adduct.

                                  TABLE II__________________________________________________________________________INGREDIENT/DESCRIPTION        VENDOR     AMOUNT (GM)                                             SOL N                                                   MOLE__________________________________________________________________________                                                   EQVN-METHYLPYRROLIDINONE         BASF       14.04    7DL-1,2-HEXANEDIOL             ALDRICH    4        2SURFYNOL 440 SURFACTANT (ETHOXYLATED                         AIR PRODUCTS                                    1.03     0.5TETRAMETHYL DECYNEDIOL)SWIRL TO MIX ORGANICS, RO WATER                         103        159.62         NAPEO                           POLYSCIENCE                                    0.0597   0.03  NADOWICIL, ROLL MILL 10 MINUTES, HOMOGENEOUS                         DOW        0.2005   0.1TRIETHANOLAMINE (TEA)         ALDRICH    4        2pH = 0.68, 70% H3PO3 pH = 7.51                         RHONE POULENC                                    1.08NEOLAN RED EXB (C.J. ACID RED 52)                         CIBA-GEIGY 1.12     0.6DUASYN BRILLIANT RED F38-SF VP218 (REACTIVE                         HEOSCHT    4.51     2.25  1RED 180)ROLL MILL 30 MINUTES, LOW FOAM                         NA         NA       NA    NApH = 7.61                     NA         NA       NA    NAINK WEIGHT = 189.41 GM, RO WATER TO 200 GM INK,                         103        10.59ROLL MILL 10 MINHOMOGENEOUS, FILTER 0.2       NA         NA       NA    NA__________________________________________________________________________ 200 GM INK FILTER TIME 0.2 MICRON 60 PSI = 330 SECONDS, VIGOROUS BUBBLE, CLEAN FILTER. LOADED KORBEL PRINT CARTRIDGE WITH 50 GM INK IMMEDIATELY PRINTED IN XPP4004. XPP4004 DRY TIME ON COURTLAND 4024DP FELT = 0.3 SECONDS.  RECOVERABILITY AFTER 1 DAY DECAPPED THEN IN XPP4004 BIPASSING LOAD PRIME = IMMEDIATE ALL JETS. NO INK WEEP NOTED. GOOD SOLID AREA COVERAGE ON XEROX TIJ TRANSPARENCY, SLIGHT CURL OF AIR DRIED SOLID AREA PRINT.

                                  TABLE III__________________________________________________________________________INGREDIENT/DESCRIPTION        VENDOR     AMOUNT (GM)                                             SOL N                                                   MOLE__________________________________________________________________________                                                   EQVTHIODIETHANOL                 ALDRICH    15       7.5GLYCERINE U.P.S.              BAKER      8.04     4DL-1,2-HEXANEDIOL             ALDRICH    4        2SURFYNOL 440 SURFACTANT (ETHOXYLATED                         AIR PRODUCTS                                    1.04     0.5TETRAMETHYL DECYNEDIOL)SWIRL TO MIX ORGANICS, RO WATER                         103        159.54         NARO WATER                      ALDRICH    4.01     2TRIETHANOLAMINE (TEA)         RHONE POLLENC                                    1.14pH = 9.99, 70% H3PO3 pH = 7.51                         POLYSCIENCE                                    0.061    0.03  NADOWICIL ROLL MILL 10 MINUTES, HOMOGENEOUS                         DOW        0.1997   0.1ENOLAN RED EXS (C.I. ACID RED 52)                         CIBA-GEIGY 1.2      0.6DUASYN BRILLIANT RED F38-SF VP218 (REACTIVE                         HEOBCHT    4.48     2.25  1RED 180)ROLL MILL 30 MINUTES, LOW FOAM                         NA         NA       NA    NApH = 7.02, 70% H3POS, pH = 7.51                         RHONE POLLENC                                    0.08INK WEIGHT = 198.63 GM, RO WATER TO 200 GM INK,                         103        1.47ROLL MILL 10 MINHOMOGENEOUS, FILTER 0.2       NA         NA       NA    NA__________________________________________________________________________ 200 GM INK FILTER TIME 0.2 MICRON 60 PSI = 5 MINUTES, DRIP TO BUBBLE, CLEAN FILTER. LOADED KORBEL PRINT CARTRIDGE WITH 45 GM INK IMMEDIATELY PRINTED IN XPP4004.  XPP4004 DRY TIME ON COURTLAND 4024DP FELT = 0.4 SECONDS. RECOVERABILITY AFTER 3 DAYS DECAPPED THEN IN XPP4004 BIPASSING LOAD PRIME = IMMEDIATE ALL JETS. NO INK WEEP NOTED. SURFACE TENSION = 27.4, VISCOSITY = 1.63, pH = 7.15

                                  TABLE IV__________________________________________________________________________INGREDIENT/DESCRIPTION        VENDOR     AMOUNT (GM)                                             SOL N                                                   MOLE__________________________________________________________________________                                                   EQVTRIMETHYLOLPROPANE            ALDRICH    14.01    7DL-1,2-HEXANEDIOL             ALDRICH    4.11     2SURFYNOL 440 SURFACTANT (ETHOXYLATED                         AIR PRODUCTS                                    0.99     0.5TETRAMETHYL DECYNEDIOL)OVEN 60C. FOR 30 MINUTES TO MELT AND MIX                         NA         NA       NA    NAORGANICSRO WATER                      103        163.95         NATRIETHANOLAMINE (TEA)         ALDRICH    4        2pH = 10.02, 70% H3PO3 pH = 7.53                         RHONE POLLENC                                    1.12PEO                           POLYSCIENCE                                    0.0601   0.03  NADOWICIL ROLL MILL 10 MINUTES, HOMOGENEOUS                         DOW        0.2009   0.1NEOLAN RED EXS (C.1 ACID RED 52)                         CIBA-GEIGY 1.2      0.6DUASYN BRILLIANT RED F38-SF VP218 (REACTIVE                         HEOBCHT    4.51     2.25  1RED 180)ROLL MILL 30 MINUTES, LOW FOAM                         NA         NA       NA    NApH = 7.63, 70% H3POS, pH = 7.52                         RHONE POLLENC                                    0.07INK WEIGHT = 194.11 GM, RO WATER TO 200 GM INK,                         103        5.89ROLL MILL 10 MINHOMOGENEOUS, FILTER 0.2       NA         NA       NA    NA__________________________________________________________________________ 200 GM INK FILTER TIME 0.2 MICRON 60 PSI = 4 MINUTES, DRIP TO BUBBLE, CLEAN FILTER. LOADED KORBEL PRINT CARTRIDGE WITH 45 GM INK IMMEDIATELY PRINTED IN XPP4004. XPP4004 DRY TIME ON COURTLAND 4024DP FELT = 0.3 SECONDS. RECOVERABILITY AFTER 3 DAYS DECAPPED THEN IN XPP4004 BIPASSING LOAD PRIME = IMMEDIATE ALL JETS. NO INK WEEP NOTED. GOOD SOLID AREA COVERAGE ON XEROX TIJ TRANSPARENCY, SLIGHT TI CURL OF AIR DRIED SOLID AREA PRINT. SURFACE TENSION = 27.3, VISCOSITY = 1.55, pH ON = 7.17

                                  TABLE V__________________________________________________________________________INGREDIENT/DESCRIPTION        VENDOR     AMOUNT (GM)                                             SOL N                                                   MOLE__________________________________________________________________________                                                   EQVSULFOLANTE (97%)              PHILLIPS 66                                    14.4     7DL-1,2-HEXANEDIOL             ALDRICH    4        2SURFYNOL 440 SURFACTANT (ETHOXYLATED                         AIR PRODUCTS                                    1.02     0.5TETRAMETHYL DECYNEDIOL)SWIRL TO MIX ORGANICS, RO WATER                         103        166.5          NATRIETHANOLAMINE (TEA)         ALDRICH    4.09     2pH = 10.23, 70% H3PO3 pH = 7.50                         RHONE POLLENC                                    1.25PEO                           POLYSCIENCE                                    0.0604   0.03  NADOWICA ROLL MILL 10 MINUTES, HOMOGENEOUS                         DOW        0.1996   0.1NEOLAN RED EXS (C.I. ACID RED 52)                         CIBA-GEIGY 1.2      0.6DUASYN BRILLIANT RED F38-SF VP218 (REACTIVE                         HEOSCHT    4.52     2.25  1RED 180)ROLL MILL 30 MINUTES, LOW FOAM                         NA         NA       NA    NApH = 7.57, 70% H3POS, pH = 7.51                         RHONE POLLENC                                    0.05INK WEIGHT = 198.93 GM, RO WATER TO 200 GM INK,                         103        3.07ROLL MILL 10 MINHOMOGENEOUS, FILTER 0.2       NA         NA       NA    NA__________________________________________________________________________ 200 GM INK FILTER TIME 0.2 MICRON 60 PSI = 210 SECONDS, DRIP TO BUBBLE, CLEAN FILTER. LOADED KORBEL PRINT CARTRIDGE WITH 45 GM INK IMMEDIATELY PRINTED IN XPP4004. XPP4004 DRY TIME ON COURTLAND 4024DP FELT = 0.3 SECONDS. RECOVERABILITY AFTER 3 DAYS DECAPPED THEN IN XPP4004 BIPASSING LOAD PRIME = IMMEDIATE ALL JETS. NO INK WEEP NOTED. GOOD SOLID AREA COVERAGE ON XEROX TIJ TRANSPARENCY, SLIGHT TI CURL OF AIR DRIED SOLID AREA PRINT. SURFACE TENSION = 27.4, VISCOSITY = 1.34, pH = 7.23

                                  TABLE VI__________________________________________________________________________INGREDIENT/DESCRIPTION        VENDOR     AMOUNT (GM)                                             SOL N                                                   MOLE__________________________________________________________________________                                                   EQVSULFOLANTE (97%)              PHILLIPS 66                                    14.37    71-CYCLOHEXYL-2-PYRROLIDINONE (CHP)                         ALDRICH    4        2SURFYNOL 440 SURFACTANT (ETHOXYLATED                         AIR PRODUCTS                                    0.99     0.5TETRAMETHYL DECYNEDIOL)RO WATER, ROLL MILL 15 MIN, MILKY SOLUTION                         103        159.89         NAPEO                           POLYSCIENCE                                    0.0593   0.03  NADOWICIL, ROLL MILL 10 MINUTES, MILKY                         DOW        0.2012   0.1SOLUTIONTRIS-(HYDROXYMETHYL) AMINOMETHANE (TRIS,                         ALDRICH    3.28     1.62MW = 121)pH = 9.93, 70% H3PO3, pH = 7.69 SOLN BECAME MORE                         RHONE POLLENC                                    1.3CLOUDY AS H3PO3 ADDEDNEOLAN RED EXB (C.I. ACID RED 52)                         CIBA-GEIGY 1.22     0.6DUASYN BRILLIANT RED F3B-SF VP218 (REACTIVE                         HEOSCHT    4.49     2.25  1RED 180)ROLL MILL 30 MINUTES, NO FOAM NA         NA       NA    NApH = 7.77                     NA         NA       NA    NAINK WEIGHT = 189.57 GM, RO WATER TO 200 GM INK,                         103        10.43ROLL MILL 10 MINHOMOGENEOUS, FILTER 0.2       NA         NA       NA    NA__________________________________________________________________________ 200 GM INK FILTER TIME 0.2 MICRON 60 PSI = 210 SECONDS, VIGOROUS BUBBLE, CLEAN FILTER. LOADED KORBEL PRINT CARTRIDGE WITH 50 GM INK IMMEDIATELY PRINTED IN XPP4004. XPP4004 DRY TIME ON COURTLAND 4024DP FELT = 0.4 SECONDS. RECOVERABILITY AFTER 1 DAY DECAPPED THEN IN XPP4004 BIPASSING LOAD PRIME IMMEDIATE 110/128 JETS NO PRINT DEFECTS NOTED. NO INK WEEP NOTED.

                                  TABLE VII__________________________________________________________________________INGREDIENT/DESCRIPTION        VENDOR     AMOUNT (GM)                                             SOL N                                                   MOLE__________________________________________________________________________                                                   EQVTRIMETHYLOLPROPANE            ALDRICH    14.01    71-CYCLOHEXYL-2-PYRROLIDINONE (CHP, LESS                         ALDRICH    4.04     2AMBER COLOR THAN PREV. LOT)SURFYNOL 440 SURFACTANT (ETHOXYLATED                         AIR PRODUCTS                                    0.99     0.5TETRAMETHYL DECYNEDIOL)RO WATER, ROLL MILL 15 MIN, MILKY SOLUTION                         103        159.97         NAPEO                           POLYSCIENCE                                    0.0607   0.03  NADOWICIL, ROLL MILL 10 MINUTES, MILKY                         DOW        0.1994   0.1SOLUTIONTRIS-(HYDROXYMETHYL)AMINOMETHANE(TRIS,                         ALDRICH    3.29     1.62MW = 121)pH = 9.85, 70% H3PO3 pH = 7.65, SOLN BECAME MORE                         RHONE POULENIC                                    1.29CLOUDY AS H3PO3 ADDEDNEOLAN RED EXB (C.I. ACID RED 52)                         CIBA-GEIGY 1.19     0.6DUASYN BRILLIANT RED F3B-SF VP218 (REACTIVE                         HEOSCHT    4.49     2.25  1RED 180)ROLL MILL 30 MINUTES, NO FOAM NA         NA       NA    NApH - 7.71                     NA         NA       NA    NAINK WEIGHT = 188.93 GM, RO WATER TO 200 GM INK,                         103        11.07ROLL MILL 10 MINHOMOGENEOUS, FILTER 0.2       NA         NA       NA    NA__________________________________________________________________________ 200 GM INK FILTER TIME 0.2 MICRON 60 PSI = 240 SECONDS, VIGOROUS BUBBLE, CLEAN FILTER. LOADED KORBEL PRINT CARTRIDGE WITH 50 GM INK IMMEDIATELY PRINTED IN XPP4004. XPP4004 DRY TIME ON COURTLAND 4024DP FELT = 0.4 SECONDS. RECOVERABILITY AFTER 1 DAY DECAPPED THEN IN XPP4004 BIPASSING LOAD PRIME IMMEDIATE 110/128 JETS NO PRINT DEFECTS NOTED. NO INK WEEP NOTED.

                                  TABLE VIII__________________________________________________________________________INGREDIENT/DESCRIPTION        VENDOR     AMOUNT (GM)                                             SOL N                                                   MOLE__________________________________________________________________________                                                   EQVSULFOLANTE (97%)              PHILLIPS 66                                    14.4     71-CYCLOHEXYL-2-PYRROLIDINONE (CHP)                         ALDRICH    10.01    5SURFYNOL 440 SURFACTANT (ETHOXYLATED                         AIR PRODUCTS                                    1        0.5TETRAMETHYL DECYNEDIOL)RO WATER, ROLL MILL 15 MIN, MILKY SOLUTION                         103        155.23         NAPEO                           POLYSCIENCE                                    0.0608   0.03  NADOWICIL, ROLL MILL 10 MINUTES, HOMOGENEOUS                         DOW        0.1994   0.1TRIS-(HYDROXYMETHYL) AMINOMETHANE (TRIS,                         ALDRICH    3.28     1.62MW = 121)pH = 9.84, 70% H3PO3 pH = 7.65 SOL'N REMAINED                         RHONE POLLENC                                    1.29HOMOGENEOUSNEOLAN RED EXB (C.I. ACID RED 52)                         CIBA-GEIGY 1.22     0.6DUASYN BRILLIANT RED F3B-SF VP218 (REACTIVE                         HEOSCHT    4.51     2.25  1RED 180)ROLL MILL 30 MINUTES, NO FOAM NA         NA       NA    NApH = 7.72                     NA         NA       NA    NAINK WEIGHT = 190.99 GM, RO WATER TO 200 GM INK,                         103        9.01ROLL MILL 10 MINHOMOGENEOUS, FILTER 0.2       NA         NA       NA    NA__________________________________________________________________________ 200 GM INK FILTER TIME 0.2 MICRON 60 PSI = 180 SECONDS, VIGOROUS BUBBLE, CLEAN FILTER. LOADED KORBEL PRINT CARTRIDGE WITH 50 GM INK IMMEDIATELY PRINTED IN XPP4004. XPP4004 DRY TIME ON COURTLAND 4024DP FELT = 0.25 SECONDS. RECOVERABILITY AFTER 1 DAY DECAPPED THEN IN XPP4004 BIPASSING LOAD PRIME IMMEDIATE 125/128 JETS NO PRINT DEFECTS NOTED. NO INK WEEP NOTED.

                                  TABLE IX__________________________________________________________________________INGREDIENT/DESCRIPTION        VENDOR     AMOUNT (GM)                                             SOL N                                                   MOLE__________________________________________________________________________                                                   EQVTRIMETHYLOLPROPANE            ALDRICH    14       71-CYCLOHEXYL-2-PYRROLIDINONE (CHP, LESS                         ALDRICH    10.01    5AMBER COLOR THAN PREV. LOT)SURFYNOL 440 SURFACTANT (ETHOXYLATED                         AIR PRODUCTS                                    1        0.5TETRAMETHYL DECYNEDIOL)RO WATER, ROLL MILL 15 MIN, MILKY SOLUTION                         103        154.9          NAPEO                           POLYSCIENCE                                    0.0605   0.03  NADOWICIL, ROLL MILL 10 MINUTES, MILKY                         DOW        0.2002   0.1SOLUTIONTRIS-(HYDROXYMETHYL)AMINOMETHANE(TRIS,                         ALDRICH    3.27     1.62MW = 121)pH = 9.87, 70% H3PO3 pH = 7.70, SOL'N REMAINED                         RHONE POLLENC                                    1.24CLEAR AS H3PO3 ADDEDNEOLAN RED EXB (C.I. ACID RED 52)                         CIBA-GEIGY 1.2      0.6DUASYN BRILLIANT RED F3B-SF VP218 (REACTIVE                         HEOSCHT    4.51     2.25  1RED 180)ROLL MILL 30 MINUTES, NO FOAM NA         NA       NA    NApH - 7.78                     NA         NA       NA    NAINK WEIGHT = 190.14 GM, RO WATER TO 200 GM INK,                         103        9.86ROLL MILL 10 MINHOMOGENEOUS, FILTER 0.2       NA         NA       NA    NA__________________________________________________________________________ 200 GM INK FILTER TIME 0.2 MICRON 60 PSI = 240 SECONDS, VIGOROUS BUBBLE, CLEAN FILTER. LOADED KORBEL PRINT CARTRIDGE WITH 50 GM INK IMMEDIATELY PRINTED IN XPP4004. XPP4004 DRY TIME ON COURTLAND 4024DP FELT = 0.25 SECONDS. RECOVERABILITY AFTER 1 DAY DECAPPED THEN IN XPP4004 BIPASSING LOAD PRIME IMMEDIATE ALL JETS W/O PRINT DEFECTS. NO INK WEEP NOTED. NO PRINT DEFECTS NOTED. NO INK WEEP NOTED.

While the invention has been described with reference to particular preferred embodiments, the invention is not limited to the specific examples given, and other embodiments and modifications can be made by those skilled in the art without departing from the spirit and scope of the invention and claims.

Claims (16)

What is claimed is:
1. An ink jet printing composition containing a liquid vehicle and a colorant and a surfactant comprising 0.3 to 0.6 wt. % acetylenic polyalkylene oxide and 1 to 4 wt % quasisurfactant penetrant based on the wt. of said composition.
2. The ink jet printing composition of claim 1, wherein said acetylenic polyalkylene oxide is: ##STR2## where n+m=0 to 50.
3. The ink jet printing composition of claim 1, wherein said acetylenic polyalkylene oxide is an ethoxylated tetramethyl decynediol.
4. The ink jet printing composition of claim 1, wherein said quasisurfactant penetrant is selected from the group consisting of dl-1,2-hexanediol, 1,2-octanediol, diethylene glycol monobutyl ether, 1-cyclohexyl-2-pyrrolidinone and 2-methyl-2-propyl-1-3-propanediol and 1-butanesulfonic acid sodium salt.
5. The ink jet printing composition of claim 1, wherein said quasisurfactant is 1,2-hexanediol.
6. The ink jet printing composition of claim 3, wherein said quasisurfactant is 1,2-hexanediol.
7. An ink jet printing process, comprising causing an ink jet composition containing a surfactant comprising 0.3 to 6 wt. % acetylenic polyalkylene oxide and 1 to 4 wt. % quasisurfactant penetrant based on the wt. of said composition to be ejected in an imagewise fashion from a thermal ink jet printer onto a substrate.
8. The ink jet printing process of claim 7, wherein said acetylenic polyalkylene oxide is: ##STR3## where n+m=0 to 50.
9. The ink jet printing process of claim 7, wherein said acetylenic polyalkylene oxide is an ethoxylated tetramethyl decynediol.
10. The ink jet printing process of claim 7, wherein said quasisurfactant penetrant is selected from the group consisting of dl-1,2-hexanediol, 1,2-octanediol, diethylene glycol monobutyl ether, 1-cyclohexyl-2-pyrrolidinone and 2-methyl-2-propyl-1,3-propanediol and 1-butanesulfonic acid sodium salt.
11. The ink jet printing process of claim 7, wherein said quasisurfactant is 1,2-hexanediol.
12. A method of improving the fast dry characteristics of ink jet inks, comprising incorporating into a thermal ink jet ink composition, a surfactant comprising 0.3 to 6 wt. % acetylenic polyalkylene oxide and 1 to 4 wt. % quasisurfactant penetrant based on the wt. of said composition.
13. The method of claim 12, wherein said acetylenic polyalkylene oxide is: ##STR4## where n+m=0 to 50.
14. The method of claim 12, wherein said acetylenic polyalkylene oxide is an ethoxylated tetramethyl decynediol.
15. The method of claim 12, wherein said quasisurfactant penetrant is selected from the group consisting of dl-1,2-hexanediol, 1,2-octanediol, diethylene glycol monobutyl ether, 1-cyclohexyl-2-pyrrolidinone and 2-methyl-2-propyl-1,3-propanediol and 1-butanesulfonic acid sodium salt.
16. The method of claim 12, wherein said quasisurfactant is 1,2-hexanediol.
US08450075 1995-05-25 1995-05-25 Thermal ink jet composition Expired - Lifetime US5534050A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US08450075 US5534050A (en) 1995-05-25 1995-05-25 Thermal ink jet composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US08450075 US5534050A (en) 1995-05-25 1995-05-25 Thermal ink jet composition

Publications (1)

Publication Number Publication Date
US5534050A true US5534050A (en) 1996-07-09

Family

ID=23786667

Family Applications (1)

Application Number Title Priority Date Filing Date
US08450075 Expired - Lifetime US5534050A (en) 1995-05-25 1995-05-25 Thermal ink jet composition

Country Status (1)

Country Link
US (1) US5534050A (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5762695A (en) * 1997-01-21 1998-06-09 Xerox Corporation Fast drying inks with polyhydroxy alcohol surfactants
US5788754A (en) * 1997-03-03 1998-08-04 Hewlett-Packard Company Ink-jet inks for improved image quality
US5830264A (en) * 1996-03-29 1998-11-03 Brother Kogyo Kabushiki Kaisha Water-based recording ink composition, and ink-jet recording process
US5861056A (en) * 1995-11-13 1999-01-19 Brother Kogyo Kabushiki Kaisha Water-based magenta INK composition and ink-jet recording process employing the same
US6174357B1 (en) 1999-07-20 2001-01-16 Lexmark International, Inc. Pigment-based ink compositions
EP1333048A1 (en) * 2002-01-30 2003-08-06 Air Products And Chemicals, Inc. Glycidyl ether-capped acetylenic diol ethoxylate surfactants
US20030177945A1 (en) * 2002-03-15 2003-09-25 Everlight Usa, Inc., Ink composition for ink-jet textile printing
US20060266260A1 (en) * 2005-05-17 2006-11-30 Seiko Epson Corporation Ink for ink-jet recording
US20070076073A1 (en) * 2005-10-03 2007-04-05 Hornby John C Inkjet inks and ink sets
US20070263054A1 (en) * 2004-10-22 2007-11-15 Masahiro Yatake Inkjet Recording Ink
US20080049086A1 (en) * 2006-08-25 2008-02-28 Rolly Luanne J Inkjet ink composition
US20080092770A1 (en) * 2006-10-20 2008-04-24 Samsung Electronics Co., Ltd. Ink composition having azo-based colorant and ink set using the same
US20110269974A1 (en) * 2003-10-09 2011-11-03 Ambrx, Inc. Polymer Derivatives
US20120026257A1 (en) * 2008-03-31 2012-02-02 Casey Robertson Thermal ink jet ink composition

Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4026713A (en) * 1975-06-12 1977-05-31 International Business Machines Corporation Water based magnetic inks and the manufacture thereof
US4153593A (en) * 1974-11-18 1979-05-08 A. B. Dick Company Fluorescent ink composition for jet printing
US4299630A (en) * 1977-04-27 1981-11-10 The Mead Corporation Infrared absorptive jet printing ink
US4383859A (en) * 1981-05-18 1983-05-17 International Business Machines Corporation Ink jet inks and method of making
US4400216A (en) * 1977-08-15 1983-08-23 Basf Wyandotte Corp. Method for preparing bleed resistant lithographic inks
US4508570A (en) * 1981-10-21 1985-04-02 Ricoh Company, Ltd. Aqueous ink for ink-jet printing
US4623689A (en) * 1983-06-29 1986-11-18 Toyo Soda Manufacturing Co., Ltd. Aqueous colored polymer, process for preparing same and ink comprising same
US4627876A (en) * 1982-11-25 1986-12-09 Basf Farben & Fasern Ag Printing ink
US4914562A (en) * 1986-06-10 1990-04-03 Seiko Epson Corporation Thermal jet recording apparatus
US5019166A (en) * 1989-06-22 1991-05-28 Xerox Corporation Thermal ink jet compositions
US5106416A (en) * 1991-08-28 1992-04-21 Hewlett-Packard Company Bleed alleviation using zwitterionic surfactants and cationic dyes
US5116409A (en) * 1991-04-17 1992-05-26 Hewlett-Packard Company Bleed alleviation in ink-jet inks
US5118350A (en) * 1991-07-29 1992-06-02 Hewlett-Packard Company Dye-set for improved color quality for ink-jet printers
US5141556A (en) * 1991-06-13 1992-08-25 E. I. Du Pont De Nemours And Company Penetrants for aqueous ink jet inks
US5143547A (en) * 1991-08-26 1992-09-01 Hewlett-Packard Company Specific dye set for thermal ink-jet printing on plain and coated papers
US5145519A (en) * 1991-12-17 1992-09-08 Hewlett-Packard Company Specific dye set for thermal ink-jet printing
US5160372A (en) * 1991-06-13 1992-11-03 E. I. Du Pont De Nemours And Company Aqueous ink jet inks containing ester diol and amide diol cosolvents
US5183502A (en) * 1988-05-18 1993-02-02 Hewlett-Packard Company Water based ink for ink-jet printing
US5196056A (en) * 1990-10-31 1993-03-23 Hewlett-Packard Company Ink jet composition with reduced bleed
US5226957A (en) * 1992-03-17 1993-07-13 Hewlett-Packard Company Solubilization of water-insoluble dyes via microemulsions for bleedless, non-threading, high print quality inks for thermal ink-jet printers
US5254159A (en) * 1992-12-17 1993-10-19 Xerox Corporation Ink compositions
US5273573A (en) * 1992-08-13 1993-12-28 Hewlett-Packard Company Specific dye set for thermal ink-jet printing on paper

Patent Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4153593A (en) * 1974-11-18 1979-05-08 A. B. Dick Company Fluorescent ink composition for jet printing
US4026713A (en) * 1975-06-12 1977-05-31 International Business Machines Corporation Water based magnetic inks and the manufacture thereof
US4299630A (en) * 1977-04-27 1981-11-10 The Mead Corporation Infrared absorptive jet printing ink
US4400216A (en) * 1977-08-15 1983-08-23 Basf Wyandotte Corp. Method for preparing bleed resistant lithographic inks
US4383859A (en) * 1981-05-18 1983-05-17 International Business Machines Corporation Ink jet inks and method of making
US4508570A (en) * 1981-10-21 1985-04-02 Ricoh Company, Ltd. Aqueous ink for ink-jet printing
US4627876A (en) * 1982-11-25 1986-12-09 Basf Farben & Fasern Ag Printing ink
US4623689A (en) * 1983-06-29 1986-11-18 Toyo Soda Manufacturing Co., Ltd. Aqueous colored polymer, process for preparing same and ink comprising same
US4914562A (en) * 1986-06-10 1990-04-03 Seiko Epson Corporation Thermal jet recording apparatus
US5183502A (en) * 1988-05-18 1993-02-02 Hewlett-Packard Company Water based ink for ink-jet printing
US5019166A (en) * 1989-06-22 1991-05-28 Xerox Corporation Thermal ink jet compositions
US5196056A (en) * 1990-10-31 1993-03-23 Hewlett-Packard Company Ink jet composition with reduced bleed
US5116409A (en) * 1991-04-17 1992-05-26 Hewlett-Packard Company Bleed alleviation in ink-jet inks
US5141556A (en) * 1991-06-13 1992-08-25 E. I. Du Pont De Nemours And Company Penetrants for aqueous ink jet inks
US5160372A (en) * 1991-06-13 1992-11-03 E. I. Du Pont De Nemours And Company Aqueous ink jet inks containing ester diol and amide diol cosolvents
US5118350A (en) * 1991-07-29 1992-06-02 Hewlett-Packard Company Dye-set for improved color quality for ink-jet printers
US5143547A (en) * 1991-08-26 1992-09-01 Hewlett-Packard Company Specific dye set for thermal ink-jet printing on plain and coated papers
US5106416A (en) * 1991-08-28 1992-04-21 Hewlett-Packard Company Bleed alleviation using zwitterionic surfactants and cationic dyes
US5145519A (en) * 1991-12-17 1992-09-08 Hewlett-Packard Company Specific dye set for thermal ink-jet printing
US5226957A (en) * 1992-03-17 1993-07-13 Hewlett-Packard Company Solubilization of water-insoluble dyes via microemulsions for bleedless, non-threading, high print quality inks for thermal ink-jet printers
US5273573A (en) * 1992-08-13 1993-12-28 Hewlett-Packard Company Specific dye set for thermal ink-jet printing on paper
US5254159A (en) * 1992-12-17 1993-10-19 Xerox Corporation Ink compositions

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5861056A (en) * 1995-11-13 1999-01-19 Brother Kogyo Kabushiki Kaisha Water-based magenta INK composition and ink-jet recording process employing the same
US5830264A (en) * 1996-03-29 1998-11-03 Brother Kogyo Kabushiki Kaisha Water-based recording ink composition, and ink-jet recording process
US5762695A (en) * 1997-01-21 1998-06-09 Xerox Corporation Fast drying inks with polyhydroxy alcohol surfactants
US5788754A (en) * 1997-03-03 1998-08-04 Hewlett-Packard Company Ink-jet inks for improved image quality
US6174357B1 (en) 1999-07-20 2001-01-16 Lexmark International, Inc. Pigment-based ink compositions
EP1333048A1 (en) * 2002-01-30 2003-08-06 Air Products And Chemicals, Inc. Glycidyl ether-capped acetylenic diol ethoxylate surfactants
US6717019B2 (en) 2002-01-30 2004-04-06 Air Products And Chemicals, Inc. Glycidyl ether-capped acetylenic diol ethoxylate surfactants
CN100448829C (en) 2002-01-30 2009-01-07 气体产品与化学公司 Glycidyl ether end-capped acetylenediol ethoxylate surfactant
US20030177945A1 (en) * 2002-03-15 2003-09-25 Everlight Usa, Inc., Ink composition for ink-jet textile printing
US20110269974A1 (en) * 2003-10-09 2011-11-03 Ambrx, Inc. Polymer Derivatives
US9574048B2 (en) * 2003-10-09 2017-02-21 Ambrx, Inc. Polymer derivatives
US8556400B2 (en) 2004-10-22 2013-10-15 Seiko Epson Corporation Inkjet recording ink
US20070263054A1 (en) * 2004-10-22 2007-11-15 Masahiro Yatake Inkjet Recording Ink
US7569104B2 (en) * 2005-05-17 2009-08-04 Eiko Epson Corporation Ink for ink-jet recording
US20060266260A1 (en) * 2005-05-17 2006-11-30 Seiko Epson Corporation Ink for ink-jet recording
WO2007041628A1 (en) * 2005-10-03 2007-04-12 E. I. Du Pont De Nemours And Company Inkjet inks and ink sets
US20070076073A1 (en) * 2005-10-03 2007-04-05 Hornby John C Inkjet inks and ink sets
US20080049086A1 (en) * 2006-08-25 2008-02-28 Rolly Luanne J Inkjet ink composition
US8227524B2 (en) * 2006-08-25 2012-07-24 Hewlett-Packard Development Company, L.P. Inkjet ink composition
CN101506319B (en) 2006-08-25 2012-09-19 惠普发展公司,有限责任合伙企业 Inkjet ink composition
US7537651B2 (en) * 2006-10-20 2009-05-26 Samsung Electronics Co., Ltd Ink composition having azo-based colorant and ink set using the same
US20080092770A1 (en) * 2006-10-20 2008-04-24 Samsung Electronics Co., Ltd. Ink composition having azo-based colorant and ink set using the same
US20120026257A1 (en) * 2008-03-31 2012-02-02 Casey Robertson Thermal ink jet ink composition
US8632630B2 (en) * 2008-03-31 2014-01-21 Videojet Technologies Inc. Thermal ink jet ink composition

Similar Documents

Publication Publication Date Title
US5865883A (en) Ink, ink cartridge and recording unit, ink-jet recording method and ink-jet recording apparatus
US5296022A (en) Ink-jet recording method and apparatus employing ink containing halogenated alkanol with 2 to 4 carbon atoms
US4256493A (en) Jet ink composition
US5439515A (en) Ink, and ink-jet recording method and instrument using the same
US5626654A (en) Ink compositions containing liposomes
US5151128A (en) Ink, ink jet recording method employing the same, and apparatus or tool employing the same
US5156675A (en) Ink for ink jet printing
US5658376A (en) Water-based dispersion ink for bubble jet printing and ink-jet recording method and apparatus using same
US20050204955A1 (en) Aqueous ink, ink cartridge using the same, inkjet printing method and recorded matter
US6003987A (en) Ink set recording apparatus and method using ink set having a dye that becomes insoluble when mixed with another dye
US4664708A (en) Waterfast ink jet compositions
US5062893A (en) Ink formulations by mixing anionic waterfast dyes containing two or more carboxyl groups
EP0943666A2 (en) Ink, ink set, ink cartridge, recording unit, image recording apparatus and image recording method
US7297194B2 (en) Ink jet ink and ink jet recording method
US4840674A (en) Ink compositions
US5248991A (en) Ink, ink-jet recording process recording unit, ink cartridge, and ink-jet recording apparatus employing ink
US5118351A (en) Ink, ink-jet recording process, and instrument using the ink
US4409040A (en) Ink for use in ink-jet printer
US5116409A (en) Bleed alleviation in ink-jet inks
US5769930A (en) Ink composition for ink jet recording and recording process using same
US4789400A (en) Waterfast ink jet compositions and process
US6025412A (en) Colored particulates for ink jet inks
US5637140A (en) Water-based ink composition and ink-jet recording process
US5256194A (en) Color ink jet recording method
US6114411A (en) Ink composition for ink jet recording and ink jet recording process

Legal Events

Date Code Title Description
AS Assignment

Owner name: XEROX CORPORATION, CONNECTICUT

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:GUNDLACH, KURT B.;REEL/FRAME:007515/0971

Effective date: 19950524

FPAY Fee payment

Year of fee payment: 4

AS Assignment

Owner name: BANK ONE, NA, AS ADMINISTRATIVE AGENT, ILLINOIS

Free format text: SECURITY INTEREST;ASSIGNOR:XEROX CORPORATION;REEL/FRAME:013153/0001

Effective date: 20020621

AS Assignment

Owner name: JPMORGAN CHASE BANK, AS COLLATERAL AGENT, TEXAS

Free format text: SECURITY AGREEMENT;ASSIGNOR:XEROX CORPORATION;REEL/FRAME:015134/0476

Effective date: 20030625

Owner name: JPMORGAN CHASE BANK, AS COLLATERAL AGENT,TEXAS

Free format text: SECURITY AGREEMENT;ASSIGNOR:XEROX CORPORATION;REEL/FRAME:015134/0476

Effective date: 20030625

REMI Maintenance fee reminder mailed
SULP Surcharge for late payment

Year of fee payment: 7

FPAY Fee payment

Year of fee payment: 8

AS Assignment

Owner name: SAMSUNG ELECTRONICS CO., LTD., KOREA, REPUBLIC OF

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:XEROX CORPORATION;REEL/FRAME:015687/0884

Effective date: 20050113

AS Assignment

Owner name: XEROX CORPORATION, CONNECTICUT

Free format text: RELEASE OF PATENTS;ASSIGNOR:JP MORGAN CHASE BANK, N.A.;REEL/FRAME:016408/0016

Effective date: 20050330

FPAY Fee payment

Year of fee payment: 12

AS Assignment

Owner name: XEROX CORPORATION, NEW YORK

Free format text: RELEASE OF SECURITY INTEREST;ASSIGNOR:BANK ONE, NA;REEL/FRAME:033100/0582

Effective date: 20030625

AS Assignment

Owner name: XEROX CORPORATION, NEW YORK

Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:JPMORGAN CHASE BANK, N.A.;REEL/FRAME:034474/0560

Effective date: 20061204